Siesta Key vacation rentals

We found 6,335 vacation rentals — enter your dates for availability

Discover a selection of 798 homes, 218 apartments, and other vacation rentals in Siesta Key that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.
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Find out more about Siesta Key

Find out more about Siesta Key

Why visit Siesta Key

  1. Beautiful Beaches: Siesta Key Beach boasts soft, powdery sands perfect for family outings and relaxation.
  2. Charming Village: Explore Siesta Key Village, filled with friendly locals, vibrant art, and unique shops.
  3. Diverse Accommodations: Choose from a range of vacation rentals, from private homes to cozy condos, all with beach access.
  4. Outdoor Activities: Enjoy family-friendly activities, including water sports, parks, and scenic outdoor adventures.
  5. Relaxing Atmosphere: Experience the perfect blend of tropical vibes and serene relaxation in this idyllic destination.

Popular types of accommodation in Siesta Key

Discover the charm of Siesta Key with our diverse selection of vacation rentals. Whether you prefer a private vacation home, a cozy condo, or a spacious apartment, we have options to suit every traveller. With beach access and a focus on transparency and savings, our Siesta Key vacation rentals promise a memorable getaway. Explore your options and find the perfect spot for your next family adventure or romantic retreat.

  • Houses: The top choice for visitors in Siesta Key, these homes offer spacious and comfortable settings for families, friends, or couples.
  • Condos: A popular option for those seeking convenience and amenities, condos in Siesta Key provide a blend of comfort and luxury.
  • Apartments: Ideal for solo travellers or couples, apartments offer a cozy and intimate setting during your stay.
  • Villas: For a touch of elegance, villas provide upscale accommodations with private spaces and stunning views.
  • Cottages: Charming and quaint, cottages offer a homely atmosphere, perfect for a relaxing getaway.**

Top attractions in Siesta Key

Siesta Key is the perfect destination for a beach getaway, offering a range of family-friendly outdoor activities. Visitors can explore beautiful beaches, urban parks, and vibrant streets, catering to those seeking both relaxation and city experiences. Consider booking beachfront rentals for a memorable stay, and don’t miss out on the opportunity to enjoy a classic beach vacation while soaking up the sun in this charming Florida locale.

  1. Siesta Key Beach: Renowned for its powdery white sand and crystal-clear waters, Siesta Key Beach offers a quintessential beach experience. Relax, sunbathe, or partake in beach activities while enjoying the vibrant atmosphere.
  2. St. Armands Circle: Just 4.8km from Siesta Key, this charming street boasts upscale shops, delightful restaurants, and a lively ambiance. Perfect for leisurely strolls and indulging in local cuisine.
  3. Point of Rocks: Nestled within Siesta Key, this unique rocky outcrop features stunning coastal scenery and excellent snorkeling opportunities, allowing you to explore vibrant marine life.

Things to do recommended for couples

For a romantic getaway in Siesta Key, indulge in luxury at The Oaks Club, enjoy captivating performances at Beatrice Friedman Symphony Center, or embrace adventure at Evie's Golf Center for a fun round of mini-golf. Each experience offers a unique way to connect as a couple.

Things to do recommended for families

Your family vacation in Siesta Key will be filled with fun activities! Enjoy a game at Ed Smith Stadium, unwind at the Robert L. Taylor Community Complex, and explore the beautiful Canopy Walkway and Boylston Nature Trail for a day of outdoor adventure.

Things to do recommended for groups

Groups visiting Siesta Key can enjoy a night at the Van Wezel Performing Arts Hall for a cultural experience, hike the scenic Sarasota BayWalk for outdoor adventure, or tee off at Stoneybrook Golf & Country Club for a fun day of sports in the sun.

What do I need to keep in mind when booking a vacation in Siesta Key

When planning your trip, whether you're traveling with a group, family, or pets, or seeking extended stays, it's important to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Siesta Key with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Siesta Key with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Siesta Key: For many families, a trip wouldn't be the same without their beloved pets accompanying them. If that resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Siesta Key: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Siesta Key

Siesta Key, a stunning island destination in Florida, offers a perfect blend of relaxation and tropical vibes. Explore the charming Siesta Key Village, where friendly locals and vibrant art create a welcoming atmosphere. Enjoy the soft sands of Siesta Key Beach, ideal for family-friendly outings. With a variety of vacation accommodations available, your stay promises scenic beauty and outdoor adventures that will leave you rejuvenated and inspired.

  • Sarasota: Sarasota is a vibrant city located approximately 8.0km from Siesta Key, offering visitors a delightful blend of beach and urban experiences. Known for its stunning sandy beaches and family-friendly attractions, Sarasota features a lively downtown area filled with shopping centres, restaurants, and cultural venues. Highlights include the Ringling Museum of Art and the Selby Botanical Gardens, both of which showcase the region’s artistic and botanical treasures. Whether you're looking to relax on the beach or explore the local arts scene, Sarasota has something for everyone.
  • Siesta Key Village: Siesta Key Village is a charming neighbourhood situated within the Siesta Key area, making it an ideal spot for those seeking a beachy, laid-back atmosphere. The village is known for its delightful shops, restaurants, and recreational areas, all within walking distance of the famous Siesta Beach. Families can enjoy the urban parks and engage in various outdoor activities, while foodies will appreciate the diverse dining options. The vibrant atmosphere, combined with the beautiful beach, makes Siesta Key Village a perfect destination for relaxation and family fun.
  • Aloha Kai: Aloha Kai is a scenic neighbourhood nestled in the Siesta Key area, celebrated for its outdoor experiences and family-friendly activities. Visitors can explore nearby beaches, take part in recreational activities, or enjoy a performance at a local theatre. The area also offers opportunities for golfing, making it a great choice for both relaxation and adventure. With its lush surroundings and proximity to family-friendly beaches and urban parks, Aloha Kai provides an inviting atmosphere for visitors looking to immerse themselves in Florida's natural beauty.

Best time to go to Siesta Key

If you're planning a trip to Siesta Key, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in January, March and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly SunnyModerately HighSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyAverageAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately HighSlightly High
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyAverageSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new journeys, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are now neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Why people love visiting lively Siesta Key

Enjoy the live music and other features of Siesta Key. Well known for its beaches, seaside and sporting events, this relaxing city won't disappoint. Siesta Key Beach and Lido Beach are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Siesta Key

Are you hoping to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Siesta Key a fun spot to vacation. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Mote Marine Laboratory & Aquarium (4.1 mi / 6.6 km)
  • Premier Sports Campus at Lakewood Ranch (15.7 mi / 25.2 km)
  • Sarasota National Golf Course (20.7 mi / 33.4 km)
  • Islandside Golf Course at Longboat Key Club (4.3 mi / 6.9 km)
  • Harborside Golf Course at Longboat Key Club (4.3 mi / 7 km)
  • Stoneybrook Golf & Country Club (6.5 mi / 10.5 km)

Exploring the beaches and other natural features in Siesta Key

Travelers enjoy Siesta Key for its sunsets, seaside and tropical locale. Whether you're an adventurous traveler or just want to take in the scenery, Siesta Key is a great place to get outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Siesta Key Beach (0.9 mi / 1.5 km)
  • Lido Beach (2.4 mi / 3.9 km)
  • Venice Beach (14.1 mi / 22.7 km)
  • Shell Beach (1.6 mi / 2.6 km)
  • Crescent Beach (2.3 mi / 3.8 km)
  • Point of Rocks (2.7 mi / 4.3 km)

Seasonal weather in Siesta Key

If warm-weather activities are high on your list, August, July, September and June are the hottest months to visit, when temperatures average 82°F.

Transportation to and around Siesta Key

The nearest airport is in Sarasota-Bradenton Intl. Airport (SRQ), located 7.8 mi (12.5 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Siesta Key?
The most in-demand types of vacation rentals in Siesta Key are condos. Want something different? Vrbo has plenty of options to match the needs of our guests, so you’ll see vacation properties in all sizes, and for all budgets. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in Siesta Key?
The average price for a vacation home in Siesta Key is determined by a number of factors, such as length of stay, property type and season. Whether you’re thinking about a sprawling villa with space for the whole family or a cozy cabin for just you and the kids, just enter your travel dates to see stays that offer great value.
How much does it cost to rent a beach house in Siesta Key?
Prices for beach houses in Siesta Key can vary depending on the size and type of the property and time of year you’re traveling. All you have to do is enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use the filters to narrow your search by ratings, amenities and more.
What are popular rental amenities in Siesta Key?
An electric car charging station, tennis and a garden top the list of most popular rental amenities in Siesta Key. Whether you plan to travel solo, with your spouse or a group of friends, Vrbo can help you find a vacation rental that fits your style with all the features you need.
What are the top attractions for families in Siesta Key?
Keep your kids busy at these leading family-friendly attractions in Siesta Key:

  • Siesta Key Beach
  • Lido Beach
  • Turtle Beach

Can I find two-bedroom vacation rentals in Siesta Key?
Gather your loved ones and enjoy a relaxing escape in one of the 1,076 two-bedroom vacation properties Siesta Key has to offer.
Are there vacation rentals with WiFi in Siesta Key?
Whether you’d like to keep up with the headlines, write a few emails or surf social media, there are 403 vacation homes with WiFi in Siesta Key. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How old do you have to be to rent a vacation rental in Siesta Key?
We recommend checking with the Siesta Key vacation home you’re looking at on Vrbo as age restrictions differ. However, it’s generally 16, 18 or 21.
How long can I rent a vacation rental in Siesta Key for?
It really depends on the Siesta Key property. To see all available options offering extended stays, simply type your travel dates and number of people into Vrbo’s search page. You can look forward to having the entire place to yourself, along with the comforts of home like air conditioning, a fully-equipped kitchen and outdoor spaces to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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